Bloomberg is throwing millions at his favorite candidates and causes — and it’s not working.

‘Of all tyrannies,” C. S. Lewis wrote mordantly in God in the Dock, “a tyranny sincerely exercised for the good of its victims may be the most oppressive.” New Yorkers might nod appreciatively at this sentiment, for in his political maturity this is the sort of tyrant that outgoing mayor Michael Bloomberg fitfully became. Bored and superfluous in a mistaken third term, Bloomberg took to focusing on the picayune and the frivolous, in a style that was unlikely to win him many friends. It is, after all, one thing to tell people in detail how they must live, and quite another to imply that their opposition is a sign of unseriousness. And the latter conviction is one that Bloomberg is not afraid to share with his critics.

Motivated consciences are hard to quiet at the best of times. Those that are animated by an authoritarian instinct and an experience of power and that are backed up by a net worth equivalent to the GDP of Paraguay are especially so. Office or no office, Bloomberg wants to do — and nothing as prosaic as the lack of popularity or effectiveness is going to stop him.

It is hard to imagine what would. His style appears to have sparked such an electoral backlash that an unreconstructed Marxist who ran in open rejection of the last two decades of municipal wisdom was able to win almost 70 percent of the vote in a city that should know better. Yet Bloomberg does not appear to feel chastened. Instead, as his term has petered out, he has merely shifted his gaze, resolving calmly that if he can no longer be the King at home, then he will become the Kingmaker abroad. A recent Time cover story simply titled “Michael Bloomberg Wants to Be Mayor of the World” laid out the path the mayor intends to take in retirement, which among other things includes spending $400 million of his own money to support Planned Parenthood, fund gay-marriage initiatives at the state level, and “back candidates who would further gun control and education.” Eight million subjects have not proven enough for the man they nicknamed Napoleon. The wider empire beckons.

Thus far, however, Bloomberg has had little in the way of success. In September, he poured $350,000 into fighting two pro-gun recall efforts in the state of Colorado. He failed. Mocked by the NRA for “wasting his money,” and by conservatives who observed with glee that a grassroots effort led by a plumber managed to unseat the sitting state-senate president and radically shift the balance of power in Denver, Bloomberg put on a brave face and declared victory anyway. But his indignation didn’t ring true. Angela Giron, one of the two state senators who were removed from office, had told TheNew Republic before the vote that if Bloomberg’s Mayors Against Illegal Guns were to “lose even one of these seats, they might as well fold it up.” “They understand that,” Giron said.

If they didn’t “understand that” then, one presumes they do now. On Tuesday, anti-gun candidates that Bloomberg backed lost mayoral races in North Carolina, Florida, and Pennsylvania — all to pro–Second Amendment challengers. In Virginia, meanwhile, Bloomberg’s super PAC shoved a million dollars into a series of television ads against attorney-general candidate Mark Obenshain. The spots focused specifically on the issues dear to Bloomberg: abortion rights and gun control. Obenshain’s opposition to abortion, his steadfast objection to background checks on private sales, and his vote to repeal the state’s defunct one-gun-a-month law all came under fire in the Bloomberg-funded ads. And yet Obenshain appears to have won anyway. Bloomberg also backed Kathleen Murphy, a Democrat in Virginia’s 34th district who incessantly criticized her opponent for failing to support gun control. Murphy lost.

MSNBC’s Chuck Todd reported this week that Democratic officials in Virginia were frustrated with Bloomberg’s interference and had wondered aloud whether the involvement of their benefactor had hindered rather than helped efforts. Ken Cuccinelli, who drew Bloomberg’s fire, lost, yes. But he lost by a much smaller margin than the polls and the pundits had predicted. Like Colorado, Virginia may well be a “purple state,” yet it has remained deeply conservative on the thorny question of firearms law. Fifty-one percent of Virginians have a favorable impression of the NRA, with just 38 percent opposing. “Already heard from one nat’l Dem who quietly worries that Bloomberg’s gun ads late were not helpful and added to closeness,” Todd tweeted on Tuesday evening.

In other political areas, Bloomberg’s luck has been no better. Ending what was one of the most significant — albeit least reported — stories of the election cycle, Coloradans this week rejected Amendment 66, a proposal that the state’s governor, John Hickenlooper, had described grandly as “the most comprehensive education-reform initiative in the history of the United States.” Bloomberg’s “Philanthropies” group backed Amendment 66 with millions of dollars; if passed, the law would have raised taxes in the state by around a billion dollars and switched out Colorado’s flat-rate income tax for one with two tiers. The proposal bombed. Sixty-five percent of voters rejected it, and even in progressive Denver, the electorate split straight down the middle on the measure. As with the recalls last September, the advocates of liberty were wildly outspent. As with the recalls, they prevailed anyway. Kelly Maher, who led the fight against the measure, drily channeled Churchill, noting brutally, “Never has so much been spent to accomplish so little.”

Observers of the scene like to talk about politicians’ having “moments.” Churchill himself benefited greatly from timing in 1940, as had Franklin Roosevelt eight years earlier. The confluence of a prosecutor’s personality and the 1993 Crown Heights riot almost certainly propelled Rudy Giuliani into office, and the horrors of 9/11 allowed Bloomberg to take the baton at the end of Giuliani’s two terms. Cometh the hour, cometh the man, the old proverb says. Twelve years later, the current hour most certainly isn’t Bloomberg’s to catch — but he has a big checkbook and an insatiable desire, and he’s going to try anyway.